Chacon-Teran, Miguel A. and Landaeta, Vanessa R. and Wolf, Robert and Rodriguez-Lugo, Rafael E. (2023) Regioselective Rhodium-Catalyzed 1,2-Hydroboration of Pyridines and Quinolines Enabled by the Tris(8-quinolinyl)phosphite Ligand. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 26 (29). e202300267. ISSN 1434-1948, 1099-0682
Full text not available from this repository. (Request a copy)Abstract
A Rh(I) complex [& kappa;(2)(P,N)-{P(Oquin)(3)}RhCl(PPh3)] (1) bearing the P,N ligand tris(8-quinolinyl)phosphite, P(Oquin)(3), has been synthesized and structurally characterized. The molecular structure of complex 1 shows that P(Oquin)(3) acts as a bidentate P,N chelate ligand. Reactivity studies of 1 reveal that the triphenylphosphine ligand can be replaced by Pcy(3) or removed upon oxidation with concomitant coordination of a second 8-quinolyl unit of P(Oquin)(3). In addition, the Rh(III) complex [RhCl2{OP(Oquin)(2)}] (3), resulting from treating 1 with either wet CDCl3 or, sequentially, with HCl and water, was identified by X-ray diffraction analysis. Complex 1 catalyzes the 1,2-regioselective hydroboration of pyridines and quinolines, affording N-boryl-1,2-dihydropyridines (1,2-BDHP) and N-boryl-1,2-hydroquinolines (1,2-BDHQ) in high yield (up to >95 %) with turnover numbers (TONs) of up to 130. The system tolerates a variety of substrates of different electronic and steric nature. In comparison with other transition-metal-based hydroboration catalysts, this system is efficient at a low catalyst loading without the requirement of base or other additives.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC HYDROGENATION; COORDINATION CHEMISTRY; SILYLATIVE REDUCTION; HYDROBORATION; HYDROSILYLATION; COMPLEXES; 1,2-DIHYDROPYRIDINES; 1,4-HYDROBORATION; DEAROMATIZATION; REACTIVITY; Chelates; Hydroboration; Phosphites; Reaction mechanisms; Rhodium |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Arbeitskreis Prof. Dr. Robert Wolf |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Mar 2024 08:51 |
| Last Modified: | 20 Mar 2024 08:51 |
| URI: | https://pred.uni-regensburg.de/id/eprint/60264 |
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